


Boss

by Badassium1970



Series: Small Dick Ross [3]
Category: Game Grumps
Genre: Blow Jobs, Boss Kink, Deepthroating, Established Relationship, M/M, Masturbation, Polyamory, Small Dick Ross, Small Penis, small penis humiliation
Language: English
Status: Completed
Published: 2017-12-12
Updated: 2017-12-12
Packaged: 2019-02-13 23:51:10
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 4,143
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/12995232
Author URL: https://archiveofourown.org/users/Badassium1970/pseuds/Badassium1970
Summary: Dan and Brian want to make one of Ross' fantasies come true, and it starts with Arin's boss kink.





	Boss

Ross never expected to end up with someone who was okay with the fact that he had a small dick. He’d been through too many times where someone has dumped him for that reason and had given up, but somehow, he now had two boyfriends who loved him, and loved the fact that he had a small cock.

At first, he was afraid that things weren’t going to work out, especially with Dan since he’d always confirm that he was heterosexual, and although he had become more comfortable with joking about his sexuality, Ross had never thought of Dan being anything other than heterosexual. Dan admitted that he was surprised as well, and that he was scared, but he had feelings for both Ross and Brian, and thinking back, he felt that he’d had those feelings for a while, but he never let himself dwell on them.

It had been almost four months and things were going well, and with Ross’ birthday coming up in a little more than a month, Brian and Dan had come up with an idea to fulfil one of Ross’ biggest fantasies. They needed his permission and the permission of others but they hoped it would fall through.

Brian already knew that Ross liked the idea of being humiliated in front of everyone at the office, and Dan had been introduced to Ross’ fantasy about a month into their relationship. He thought he would be jealous, but the idea of everyone having their way with Ross and humiliating him was apparently a massive turn on. Dan wondered if it was some kind of revenge for all the times Ross had irritated him. The pair had come up with the idea of letting everyone else have sex with Ross once during the weeks leading up to his birthday, and then a couple days before they would all take part in humiliating Ross.

“So an orgy?” Dan questioned, raising an eyebrow.

“I thought that was obvious enough that you wouldn’t need clarification, but yes an orgy,” Brian rolled his eyes when Dan giggled, for some reason finding Brian saying the word ‘orgy’ amusing.

They were both nervous bringing the idea up to Ross, afraid that he may not like the idea, and would possibly be angry with them for suggesting it considering he had been so insecure about his size, and that he may think they were just fetishizing him.

“Do… do you think they’d be willing?” Ross asked when the proposition was made. While he was scared that things could go badly, and he could ruin friendships and make work really awkward, the fact that things had gone well with Brian and Dan had given him more confidence.

“Well I’m pretty sure Arin was checking you out when he caught us a week ago,” Brian smirked. That was what had given him the idea to actually try and fulfil Ross’ fantasy. Dan and Ross both blushed, still embarrassed that Arin had caught them, especially since it was at the office. They had thought everyone had left, but obviously not.

“You sure? He could have been looking at Dan,” Ross suggested, still a little unwilling to believe that someone would view him in that way considering his short-comings.

“Dude, I’m pretty sure if Arin was going to actually make a move on me he would have done it years ago,” Dan replied, knowing that it was true.

“I can’t say I know one hundred percent that he’s into you in some way, but if you're okay with us asking him if he would like to help fulfil that sexy little fantasy of yours, then we’d like to,” Brian shrugged, not really knowing where he was going with that, but he’d made his point clear.

Ross thought it over, knowing that if Arin said no, things between them could change and become very difficult, but at the same time he knew Arin, and knew that Arin wasn’t really one to let that happen. He wouldn’t want to lose a friend just because of something they fantasized about.

“I mean, sure why not,” Ross said, trying to act natural but he couldn’t keep a smile off of his face, and he was getting hard just at the thought of actually getting to live out this scene he’d pictured in his head. He hoped it wasn’t noticeable, embarrassed at how easily excited he got just thinking about it.

“Sweet, now let’s take care of your little ‘problem’,” Dan smirked, wrapping his arms around Ross from behind, and grabbing at the front of Ross’ pants, grinding against Ross’ ass to show that he was also hard. Dan still hadn’t actually had sex with Ross yet, not yet comfortable but he didn’t mind dry humping him, even if it did make him cum in his pants one time, something Brian still hasn’t let him live down.

Speaking of Brian, he was currently just watching the two, proud of his two boyfriends because they had both been so scared and unsure at first, but now they were a lot more confident, shown by the way Ross agreed to ask Arin and how Dan was taking charge in sexual situations. It was a weird thing to be proud of, but he really was proud of them, and glad that they were comfortable and happy.

That night Brian showed Dan and Ross how proud of them he was.

The next day they agreed that they would talk to Arin after work. Dan and Arin were recording, so they would probably be the last to leave anyway. Arin was a little nervous when Dan asked if he could talk with Arin about something, especially when he went on to say that it was also concerning Brian and Ross. He hoped that the three weren’t having problems, or caught him staring. He had felt so guilty jerking off to the thought of the three of them, but that guilt fading slightly when they told him what they wanted.

“You want me to what?” Arin questioned, not quite believing what he was hearing.

Ross’ face was already bright red, and he didn’t think he could say it again. Dan was almost as red as Ross was. Luckily Brian wasn’t as noticeably phased.

“We had this idea for Ross’ birthday, and we were wondering if you wanted to be part of it; y’know considering how you were looking at Ross the other day,” Brian gave Arin a knowing look as a way to make sure Arin didn’t try to lie his way out of this.

“Eh…I…I mean…” Arin stammered, unsure of whether this was just a way of catching him out.

“Arin, if… if you don’t want to, it’s… it’s fine,” Ross spoke, his voice soft, sounding a little defeated. His tone was what made Arin believe this was real, because he knew when Ross used that voice he was afraid of being hurt, but trying to put on a brave face.

“No, no I want to,” Arin replied quickly, probably sounding way to eager but he didn’t care. When Ross used that tone it always reminded him of the times he had been a dick to Ross when they were teenagers.

“Knew it,” Brian grinned, holding up his hand to hi-five Dan, who rolled his eyes but still, reluctantly, returned the hi-five.

They agreed for Arin to meet them at Ross’ house in a couple of days, giving Arin more time to think about it and back out if he needed to, which the three told him was totally okay. It was also just a convenient day for all of them. Ross was nervous, yet excited. He was also scared that he might not actually like acting on the fantasies, and that they were better in his head.

“That’s why we’re going to be in the guest room, in case you need us,” Dan reminded Ross when he explained how he was feeling. They had it planned out that Arin and Ross would do a scene together, the topic already discussed, though Ross wasn’t made aware of it, he just knew it was something that he liked. Dan and Brian would make sure they were close by just in case anything went wrong, not that they thought it would, but they wanted to be safe rather than sorry.

“Okay, I think I’m ready,” Ross said smiling.

“Good cuz I think I just heard Arin’s car pull up,” Brian replied, giving Ross a quick kiss on the forehead before getting up to open the door for Arin.

Ross was glad that Arin seemed just as nervous as he was; face slightly red and a shy yet goofy smile on his face. The four skipped pleasantries, knowing it would only make things more awkward. Instead, they walked to the bedrooms, Dan and Brian going into the guest bedroom, while Ross and Arin went into the master bedroom.

When they were in the bedroom Ross felt his nerves building and he felt really hot all of a sudden. Arin could tell Ross was feeling a little uncomfortable and was quick to help him.

“Hey, you know I want to do this right? But y’know, if it doesn’t go well or you don’t want to I’m okay with that,” Arin shrugged, showing that it wasn’t a big deal. Ross was thankful that Arin was able to remain calm and his words helped Ross feel more confident and comfortable.

“Yeah, I want this to,” Ross stated, his voice a little shy. He was still a little afraid to tell people what he wanted, sexually at least, but Arin was his friend and agreed to this, which made things a little easier.

Smiling Arin wrapped his arms around Ross, his hands travelling down to gently squeeze at Ross’ ass which made Ross let out a high-pitched whine.

“Good, cuz remember I am your boss,” Arin began, moving from there embrace so that he could start undoing his belt, his eyes on Ross the whole time, taking in his reaction.

Ross’ eyes widened at what Arin had just said and he felt himself grow increasingly harder. He’d always had a bit of a boss kind and he wondered if Dan and Brian had made Arin aware of this. If they did then he honestly didn’t mind. Arin seemed confident in what he was saying, a major change in his demeanour compared to just a few seconds ago, making Ross wonder if Arin had done this before, or if it was something he was also interested in.

“I… uh, yeah, I guess you are,” Ross stammered, still surprised at what was going on. He often forgot that Arin was technically his boss, and while he had a boss kink Ross rarely thought about Arin being his boss.

“I am your boss Ross, and you know I could fire you,” Arin stated, his voice firm, and slightly cold. 

“F-fire me? What for?” Ross questioned, still struggling to talk. His mouth felt dry and he was way too aware of his erection.

“Well, I did catch you, Dan, and Brian fucking at the office. In fact, maybe I should fire all of you,” Arin’s tone was harsh and definite. While this would normally scare Ross, instead it just turned him on more. This was one of his best friends, but in this moment Arin was nothing but his boss, and that did nothing but arouse Ross further.

“I guess firing Dan might make things difficult, but Barry could take on his role I guess. What do you think Ross?” Arin folding his arms, stood there with his belt undone and the zipper of his jeans seemed to somehow be accentuated, but maybe that was just in Ross’ head, but he knew what he had to do.

“Arin, you, you can’t fire them. Please, I… I’ll do anything,” Ross hung his head in submission.

Arin took a step towards Ross, placing a finger under Ross’ chin to tilt his head up.

“I guess I could find a use for you,” he whispered before unzipping his jeans, letting them fall to the floor, revealing that he wasn’t wearing boxers.

“Get on your knees bitch,” Arin hissed in Ross’ ear, and he felt his cock twitch at the delightful little chocked off moan Ross struggled to keep in. He loved the way Ross looked on his knees, looking up at him. He knew they shouldn’t be doing this, if it was any other business it would probably be wrong, but Arin didn’t care. He was in the right headspace now, and Ross was no longer his friend, but his employee and Arin was just his boss, who was currently jerking off above Ross until he was fully erect. He was just about to tell Ross to start sucking him off when he saw the clock that was hanging on the wall in front of him, which gave him an idea.

“You have ten minutes, if you don’t make me cum in that time then you and your boyfriends are all fired,” Arin asserted, glaring slightly at Ross to try and make it seem like he was more serious about it.

Ross waited until Arin told him that his time had started before slowly leaning in to give Arin’s cock a few experimental licks, trying to find out where Arin was most sensitive so he could use that as his advantage. He wanted to make Arin cum. He wanted to make his boss cum. He wanted to swallow his boss’ cum and make his boss proud of him.

“A minute’s already u-up, if th-that’s the best you can do, you can kiss your job go-goodbye,” Arin tried to keep his voice firm but Ross really did know what he was doing with his tongue.

Arin began to regret speaking when Ross decided to pick up the pace, instantly deep-throating Arin like it was nothing. He had forgotten that Ross barely had a gag reflex, and while he was thankful for it he also wanted to last longer, drawing out this scene he had created.

A little over five minutes had passed, and Arin knew he was close to cumming. Looking down at Ross didn’t help. He was completely dishevelled, hair a mess, mouth stretched wide around Arin’s thick cock, a little bit of drool running down his chin. Ross was moaning around Arin’s cock, and Arin wasn’t sure if they were fake or not, but the vibrations were bringing him closer to the edge and he needed to stop for a moment. He didn’t want to cum until it had almost been ten minutes.

Arin tugged on Ross’ hair slightly, not enough to hurt because they hadn’t discussed that beforehand. Ross got the hint and moved back, but not before giving the tip of Arin’s cock one last lick, making Arin’s whole body shiver. While he feared that he might have done something wrong, or that ten minutes had passed quicker than he realised, Ross was kind of glad to take a break since his jaw was beginning to hurt. Arin’s cock was thicker than Brian and Dan, and while Ross had once tried to suck both of them off at the same time a few times, he wasn’t used to the feeling of something so big in his mouth.

“Y’know, when I walked in on you and your boyfriends I was surprised to see how small you are. In fact, sometimes I think I must have been seeing things, because there’s no way your cock can be that small,” Arin spoke, looking Ross directly in the eyes. Ross could feel himself blushing, and his gaze went to the floor in a way that was almost bashful, maybe it would have been if it Arin didn’t already know that Ross had a small cock.

“Oh, maybe it is,” Arin said and Ross struggled not to roll his eyes. While Arin was doing a good job in the scene, that was a little overexaggerated.

“I think I need to see for myself, because it can’t be. Prove me wrong Ross, prove you don’t have a tiny cock.” Arin’s voice was very authoritative, letting Ross know that there was no talking his way out of this, not that Ross was even going to try.

Still kneeling on the floor Ross undid his jeans, pulling them down with his boxers, knowing that Arin would still be keeping track of time passing. His underwear was covered in an embarrassing amount of pre-cum, his cock was also covered in it. Ross could feel Arin’s eyes on his, and with slight hesitation he looked up at his boss.

Arin’s gaze was even more lustful than before, and he was slowly jerking off. He had only gotten a brief glance at Ross before, trying hard not to stare for too long, but know he could look all he wanted. The differences in their size was such a turn on, especially when comparing their girth. It also made him think about how Ross is smaller than him, shorter and lankier.

“I guess, ngh… Guess you really are that small. Thought I was seeing, fuck, seeing things,” Arin was so close, but he was trying his best to keep his dominant persona. Looking at the clock he saw that time was slipping away.

“Almost just a minute left, still think you can save your boyfriends jobs,” Arin stopped jerking himself off, ready for Ross’ mouth again. He knew he wasn’t going to last another minute, he’d be lucky to last more than ten seconds.

Ross was quick to start sucking off Arin again, this time he wasn’t playing around and being a tease; focusing on one thing and one thing only: making Arin cum.

“Fuck Ross, yo-you gonna let me cum down your throat? Gonna, uh... fuck, gonna swallow your boss’ cum?” Arin pulled out of Ross’ mouth to let his answer.

“Please, please cum in my mouth boss,” Ross begged, his voice raspy from sucking Arin’s cock.

Arin didn’t need to be told twice, and not even a few seconds after Ross was done speaking his cock was back in Ross' mouth, and Ross instantly started to deepthroat him, swallowing slightly around Arin’s cock.

Arin came with a loud moan, accidentally forgetting to warn Ross, but Ross didn’t seem to mind as he swallowed Arin’s cum. It didn’t surprise Arin, he knew Ross would do that, but that didn’t take away from how hot it was, knowing that someone who worked for him just sucked him off and swallowed his cum.

“Just in time,” Arin commented breathlessly as he looked at the clock and saw that it had only just passed ten minutes.

“Think you deserve a reward for that,” Arin continued as he pulled up his pants, zipping them up. Ross looked at Arin in confusion, but he wasn’t going to pass up a reward.

“I know you like to be humiliated, I heard what Brian and Dan were saying to you. Don’t worry their jobs are safe, and as if I’d fire you now I know what a good little cock slut you are,” Arin smirked at the way Ross whimpered at his words.

“So you’re going to jack off your tiny cock while your boss humiliates you, like the sound of that? What am I saying? Of course you do.” Even though Arin sounded confident, he gave Ross a look that told him he could back out of this if he wanted. Like hell Ross was going to back out of this, and he gave Arin a small smile and nod to show that he wanted to continue.

“You waiting for my permission? Maybe you’re a better employee than I thought. Well go on then, jerk your pathetic cock off for me,” Arin ordered and Ross was quick to comply. He knew that he should be putting on a show but he was too desperate. All he wanted to do was cum.

“Maybe I should make you do this at the office. You seem to have no problem having sex at the office anyway, so why not? Can you imagine everyone finding out that you’re not only fucking two of your co-workers, but your boss as well? Imagine what they’d think of your tiny cock. I bet you already get off thinking about that though, don’t you?”

Ross tried to answer, but his reply only came out as a loud choked moan as he came, shuddering as he painted his legs and fist with his cum.

Arin got some tissues from the bedside table and waited for Ross to come down from his orgasm before passing them to Ross to clean himself up. Ross couldn’t help but think about the fact that Brian and Dan usually helped him clean up, but he didn’t expect the same from Arin, nor did he want it. This was purely sexual.

After cleaning himself up, Ross pulled his boxers and jeans back up. He was still a little dazed from cumming, but he could tell Arin wanted to say something but felt too awkward.

“Hey Ar, you alright?” Ross hoped that this hadn’t made Arin feel uncomfortable. Maybe he had only done this to be nice.

“Yeah, sorry. I just… it’s kinda unbelievable that we did this, but it isn’t going to change anything, is it?” While Arin loved Ross, it wasn’t like that. He valued Ross’ friendship, and while he did find him attractive he didn’t want a relationship with him.

“No, nothing’s gonna change, I’m still gonna go out of my way to annoy the shit out of you but you secretly love it,” Ross joked, also feeling a little awkward, but he knew things would go back to normal soon.

“Okay cool. We should probably go check on Dan and Brian,” Arin suggested, knowing that the pair, or at least Brian, would tease them but it might help the atmosphere change and become more normal.

“Yeah, I’ll go, just in case, y’know…” Ross said, and Arin nodded, excusing himself so he could go to the bathroom and he told Ross he’d meet them in the living room.

When Ross knocked on the master bedroom door he was soon greeted by Dan, who was trying way too hard not to smile, excited for Ross. He had been a little insecure beforehand, scared that Ross may find that he likes someone else more, because they were more confident than he was in the bedroom, but Ross and Brian had quickly gotten that thought out of his head and now he was just happy that he could help make one of Ross’ fantasies come true.

“Hey man, how’d it go?” Dan asked, trying to act natural and Brian couldn’t help but roll his eyes.

Ross rubbed the back of his neck bashfully, feeling his face head up.

“It went well, Arin’s in the bathroom now, but I’ll tell you about everything later,” Ross smiled, unable to stop himself. He was actually on his way to actually doing what he had fantasied about for years now. He explained that they were going to go into the living room, he suggested watching a movie or something, and for Brian and Dan to not mention what happened unless Arin brought it up, which they agreed with considering this was a new experience for all of them. 

Arin met them in the living room and sat down next to Dan since Ross was in the middle of Dan and Brian. He didn’t mind, and didn’t plan to stay long, knowing that the three probably wanted to talk things over just in case Ross wanted to call things off, so he only stayed for fifteen minutes maybe a little less. The conversations came naturally, mainly being about work, which at first made Arin and Ross a little flustered but they quickly got over it.

“Okay, well I need to go home, but if you need to talk or anything, just call,” Arin said before getting up, and the others promised and said their goodbyes, Brian walking with him to the door, thanking him for being so open-minded about everything, and not being mad at them for having sex at the office.

“Just don’t let it happen again,” Arin sighed, but he had a smile on his face.

“No promises,” Brian smirked, his voice filled with glee and Arin made a mental note to always knock from now on.

As soon as Arin left Dan and Brian were questioning what happened, and Ross made sure not to leave out any details before excusing himself to go to sleep, leaving Dan and Brian sat watching some shitty movie, both completely hard, and they knew they would need to get revenge, and they knew just the people to go to.


End file.
